In the capitalof fashion outliers, it’s a rare outfit that succeeds in being truly transgressive. The first scandalous look to catch New Yorkers’ eyes may have been that of Lord Cornbury, the Colonial governor from 1702 to 1708, of whom it was said that he dressed “publiqly in womans Cloaths Every day.” Now, that sort of the thing wouldn’t turn a head. So much outré dressing has been ahead of the curve. As for what has not lost the power to shock: piling on the excess during lean times, and — to a much lesser extent — taking off one’s clothes.

1897

The Ball That Made Heads Spin

Bradley Martin Balll, 1897.

The Bradley Martin Ball, held at the Waldorf, was, depending on who was telling the story, either an attempt to boost the city’s economy during a recession or a bid to outdo the legendary 1883 Vanderbilt costume ball. As socialite Cornelia Bradley Martin saw it, inviting all the guests on short notice meant that they’d have to have their ensembles made in New York, as opposed to ordering them from Paris ateliers. Preachers urged their congregations not to attend; as one put it, “You rich people put next to nothing in the collection plate, and yet you’ll spend thousands of dollars on Mrs. Bradley-Martin’s ball.” The dress code decreed 16th-, 17th-, and 18th-century attire, with attendees costumed as Mary Queen of Scots, Pocahontas, and, naturally, Marie Antoinette.

Anita Loos, 1919.

1919 The Décolletage That Made Them Gasp

Four-foot-eleven Anita Loos shopped in the children’s department and was given to wearing boys’ sailor suits and lederhosen, leading Cecil Beaton to call her “the embodiment of cuteness.” But the décolleté of her dress for a ball she attended with her husband, John Emerson, was considered remarkably risqué. By the time flappers came along, the look would be commonplace.

1930 A Debut at the Ritz

The previous year’s stock-market crash did not factor into Woolworth heiress Barbara Hutton’s plans for her debutante ball at the Ritz-Carlton ballroom. Wearing an elaborate star-shaped headpiece and a white tulle dress with an over-the-top gilded neck detail, Hutton fit in perfectly with the “moonlit garden” theme. But the press did not look so favorably on her show of fashionable excess. Formerly called the Poor Little Rich Girl, she later became known as the Rich Bitch.

1974The Night Cher Was Sheer

As Bob Mackie’s date to the Met Gala, Cher wore a feather-trimmed creation by the designer that was a precursor of today’s “naked dresses.” Jewelry designer Kenneth Jay Lane, who sat across from her, remembers it vividly. “It was one of the first sheer things. You could see her nipples.”

Margaret Trudeau, 1979.

1979The Canadian South of the Border

Long before Justin Trudeau thrilled the world with his conference-table yoga poses, his mother, Margaret Trudeau, was living her truth at Studio 54, and that truth included indecent exposure. Trudeau famously left her prime-minister husband to enjoy the club scene and befriend the Rolling Stones. She supposedly spent three nights in a row at the disco mecca and “patrons noticed she was wearing nothing under her dress while she sat cross-legged on the floor signing autographs.” First Lady of Canada “Caught With No Panties!” trumpeted High Society.

Alaïa.Photo: Ron Galella

2000 The Alaïa That Was a Lepore

“I didn’t have time to borrow a dress from Alaïa” was Amanda Lepore’s excuse for her Alaïa-party ensemble, which consisted of silver high heels, a change purse, and nothing else. “After that,” she told a website recently, “showing up naked kind of became my thing.”